


Double The Trouble

by mooseilicious



Category: Supernatural
Genre: Age Difference, Alternate Universe - Student/Teacher, M/M, Pure Smut, Threesome - M/M/M
Language: English
Status: Completed
Published: 2014-03-06
Updated: 2014-03-06
Packaged: 2018-01-14 17:05:48
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 10,631
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1274344
Author URL: https://archiveofourown.org/users/mooseilicious/pseuds/mooseilicious
Summary: <blockquote class="userstuff">
              <p>Jimmy's failing his English class and needs a tutor, and whose better than the actual teacher himself?</p>
            </blockquote>





	Double The Trouble

**Author's Note:**

> An old rp I had dug up from a while ago (◡‿◡✿)

[[high school AU]]

English was one of his favorite classes, filled with literature that he enjoyed, lectures that held his interest, and a teacher that was pleasing to watch. Before class had started, he was taken aside by said teacher, with confusion written all over his face. It turned out that he was failing and his scores needed to improve in order for him to graduate. "Talk to me after class." He was told as the bell rang to start classes. And he did. Class passed by quickly, his eyes on Mr. Winchester the whole time, and before he knew it, the period was over. Students filed out of the classroom, bidding their 'goodbyes' and 'see you tomorrows' as he packed his things and went over to his teacher's desk. "Mr. Winchester?" Jimmy stood in front of the desk, fidgeting nervously with a book bag strap. "I've been thinking and.. Do you think, it's possible if you could tutor me? I haven't been studying well, as you said, and I have club activities after school usually." He looked at his teacher with wide eyes, fawning innocence as he worried over his lower lip in anticipation.

Dean looked up from the paper he was currently grading to gaze at his student, listening intently as the boy spoke. He nodded slowly when the youth had finished, and spoke in a thoughtful tone. "Yes, tutoring would be fine. Feel free to come in anytime before 4 after school, as that is when I go home. I'm glad you see the importance of getting your grades up, Mr. Novak. Getting into a good college depends on good grades." He flashed a brilliant smile before his eyes returned to his work, checking off wrong answers quickly so that the paper was done. He glanced up at the clock then, then looked up at Jimmy once more. "I suppose, since you are here now, we could get started. Do you have your failed assignments with you?"

"Actually-" He blurted right after the last word was finished, clamping his mouth shut immediately. "Sorry sir, but.. I was actually wondering if you could come to my house or something. I have swim practice in a few minutes and if I'm late, Coach will give me extra laps." Jimmy made a miserable look, casting his eyes downwards as he chewed on his lower lip. "I- I know that's asking a lot and I understand if it's not possible but.. I don't really have any other time to come in." He winced at his words, chiding himself mentally with a sigh as he shifted his weight from one foot to another.

One brow raised in contemplation before Dean nodded, smiling softly. "I have cross country practice to coach on Mondays, Wednesdays, and Fridays at 4. After 5:30, I'm free the rest of those three days. Otherwise, I'm free after 4 on Tuesday and Thursday, and all day on weekends." He paused, hoping that the student got all that. He didn't want to overload the youth's mind with information. "What time does your practice end today, Jimmy?"

The times were cataloged into his head, easily matching them with his schedule with an internal smirk that his face didn't show. "Oh um.. 5:15." That was if he got to practice on time and not a few minutes late. Jimmy glanced over at the clock and muttered under his breath. "Um.. So I guess I should give you my address then?" He swung his bag over to fish out a scrap of paper and a pen, hastily scribbling down the street and his phone number just in case. "I have to go Mr. Winchester. Coach will have my head if I'm late again. Just.. Text me or something if you're okay with tutoring me later. Thanks." The paper was slid across the desk before he turned, giving one last wave before he was running down the halls to the locker room to change.

Dean smirked as he took the slip of paper, nodding to Jimmy. "I'll be there, don't you worry," he called out as the student left. He glanced down at the paper in his hand, biting his lip as he slipped a hand into his pocket to pull out his phone. It was probably wrong to keep a student's number and address but as long as it was only for tutoring purposes, it was okay. He hoped. After saving the number in his contacts, he stuck his phone back in his pocket and sighed, glancing over at the clock. 3:15. He had two hours. He supposed he'd better get to grading then if he wanted to make it home by 4. The address Jimmy had given him was actually not too far away, so it wouldn't be hard to get there. He picked up his pen and looked down at the papers, breathing out another sigh as he began grading them.

Luck was on his side, barely, as he scampered into the locker room to shuck his clothes off and shove on his speedo. By the time he busted through the door that lead over to the pool, the coach had just began to give out the workout. Warm up, stretch, dry land workouts, and finally the actual workout later, they were dismissed. Jimmy hauled himself out of the water, taking off his swim cap and goggles as he shook his hair. 5:18, still on time kind of. He went over to the locker room to dry off quickly, missing a few spots as he took off the speedo and put on the boxers, shorts, and a shirt. The others were chatting, laughing and jeering as most showered and usually he would have been with them. Except that he had someone waiting, someone that was attractive and was his teacher. He called out his good byes and ran out the door with his bag slung over his shoulder, semi damp hair sticking up in every direction. It took a moment for him to find the older man, a breathless grin on his face as he spotted the dirty blond. "Mr. Winchester!" He called out, going up to the man with an apologetic smile. "Sorry I kept you waiting."

Dean had decided to stay even past 4; he was thinking maybe he could catch the youth before he left from practice. He was just locking up his room when he heard a voice call out his name, a familiar voice, and he turned with a wide smile on his lips as he slipped his keys into his pocket. "Ah, Mr. Novak! Perfect timing. I was wondering, did you need a ride home?" He took in the boy's spiked hair and damp clothes, amusement evident in his eyes. He met the boy's brilliant blue gaze, tilting his head slightly in question. "You look like you haven't showered yet. Did you rush over here just to meet me?"

His gaze was cast downwards, heat flaring to his cheeks as he rubbed the back of his neck. "Practice went out longer than usual and I didn't know if you'd wait or not so no. But I usually shower at home so it's okay." He cringed at the lie and how he babbled, congratulating himself with a mental sigh. "But um.. If you are coming over then, yes please?" Jimmy tried to sooth his thumping heart, taking gulps of air to not seem like he had practically raced over here. Which he did, but Dean didn't need to know to add to his embarrassment. "You are coming over right?" He asked after a moment of thought, looking up with a hinted cringe of the possible mistake of thought.

He smiled warmly at his student and patted the youth's shoulder, chuckling as he turned the young man around. "Come on, we've got a tutoring session at your place," Dean assured, steering the youth gently towards the door that led out to the teacher's parking lot. He kept his hand lightly on Jimmy's shoulder as they walked towards his car, his pride and joy: a 1967 Chevy Impala, colored black and shined to perfection. He pulled his car keys from his pocket as they ended up on the passenger side, and he quickly unlocked the door and opened it, gesturing for the student to climb in. "You can toss your stuff in the back if you'd like."

A smile stretched across his face, the corners of his eyes crinkling slightly as he bound after his teacher. The sunlight blinded him for a few seconds, his face scrunched up as his eyes adjusted to the sudden brightness. He was lead over to a car, dark and sleek, pulling a low whistle from him as he stopped by the back door. "This is your car? I thought it was someone else's." Honestly it wasn't that much of a surprise. A guy like Dean with a car like this? Figures. But he kept it to himself. Jimmy opened the door and put his bag down with a small huff, closing it and opening the passenger's side to slide in. "Do you know how to get there?"

"My baby. She was passed down to me from my dad." He chuckled as he climbed into the driver's side, shutting the door and strapping on his seat belt. "Your address actually isn't too far from my place. But just in case, you can direct me." Dean winked over at the student as he climbed in, a throaty chuckle slipping between his lips. He inserted the keys into the ignition and started up the car, smirking as he pressed on the gas pedal slightly even though it was in park, making the engine purr loudly. He glanced over at his student, raising a brow in question. "When I hit the main road to that leads to our neighborhood, I advise you to hold on tight." As soon as the youth had buckled in, Dean shifted the car into drive and pulled out of the parking spot, glad that he was one of the only few cars there. As soon as he'd hit the main road, he floored it, the engine roaring as the speedometer needle nudged past 40, and it was still going. There was barely any traffic surprisingly, which made it easy to dodge the few cars they did see. He had a grin on his face as he drove, his expression one of pure joy, and for a bit he forgot he wasn't alone in the car. He automatically slowed when they breached the first few houses, and he glanced over at Jimmy, chuckling. "Hope I didn't scare ya, kiddo."

What. Before he could do anything, speak or even breathe, they were tearing down the roads. What the _hell_? For a minute his mask fell, a glint flickering behind his eyes as his lips twitched. Then he was back to wide eyes and paled skin, hands holding onto the sides with white knuckles. So there was more to this man than the prestigious teacher that had just lectured him on getting good grades to get into college. A spark of glee shot through him as he saw the joy on Dean's face out of the corner of his eye. When they slowed down he released the leather, took a few stammered breaths and turned to stare at Dean. "That was.. Fast." He said slowly, swallowing once. "And furious." He muttered under his breath, slapping himself mentally for the lame pun. "I mean, my house is the grey one over there." Jimmy sat up in his seat and pointed over to a house.

He laughed at the pun, shaking his head slowly as he grudgingly slowed to 20 miles per hour, the speed limit for the neighborhood. "I'm not Paul Walker, but I definitely love to drive fast _And_ furious." He snickered lightly, then smiled over at Jimmy to show he was teasing. He pulled up to the curb in front of the house the youth had pointed out, taking in how nice it was. Of course, all houses in this neighborhood looked good on the outside. Usually the inside too. He put the car in park and killed the engine, leaning over towards Jimmy slightly to get a better look at the house. "My house is the same color. Almost looks exactly the same. Except mine's a bit.. thinner looking." He chuckled as he pulled back and took the keys out of the ignition before climbing out of the car, gazing at the house as he shut the door. He knew Jimmy had a twin brother- Castiel was on Dean's cross country team- and he wondered if the other boy was home. Probably, considering how late into the evening it was getting. "I hope your parents will be okay with our arrangement, Jimmy. I don't want to intrude." He frowned, worry flickering across his expression.

An expression similar to a hinted sorrow flashed across his face, covered by a small smile and a shake of his head. "I don't live with my parents, my brothers and sister take care of me." He climbed out of the car and shut the door, swinging his bag over to rummage around for his keys. "Everyone's out though, so it's okay." Jimmy went over to the front door, unlocked it and pushed the door open. "If you don't mind, I'm going to take a quick shower so I don't reek of chlorine. The kitchen's over there if you want to grab something to drink and the living room's right here." The rooms were pointed out as he toed off his shoes and walked over to the staircase. "Give me 10 minutes." With a quick smile, he darted upstairs and made a beeline to his room. 

Dean frowned, ready to apologize, but the youth had already ran up to the door and unlocked it. He followed cautiously, smiling and nodding as Jimmy spoke. The youth rushed upstairs before Dean could say anything, and he heaved a small sigh as he toed off his own shoes before heading to the kitchen, turning in a 360 to take in his surroundings. The place was beautiful, as was easily imagined, and it was a bit before he finally realized he should probably sit and wait for Jimmy to be done. He could hear the shower running upstairs and he smiled, chuckling as he sat down at the kitchen table. So Jimmy had other siblings, not just his twin. Interesting. Dean wondered if he'd seen them at all school; surely he would've noticed if others with the last name 'Novak' were in his class.

His bag was dumped in the corner as he shut his door with his foot, letting out a sigh as he took a moment to stand and scrub a hand over his face. Dean was in his house. _The_ Dean Winchester. A grin slid across his lips as he went over to his bathroom. Wait. Jimmy retraced his steps back over to his bed, tilting his head and sighing at what he found. A blue note and a box, laid neatly at the edge of his bed. Without giving it a second thought, he scooped the items up and walked back over to the bathroom, locking it to turn on the water.

A hand slipped against the shower wall, his eyes closed as he breathed deeply. Inhale.. Exhale.. Inhale... He made a small noise as his eyes snapped open, hand sliding across to lay his forearm against the cool tiles to support his weight. Suds dripped down from his hair and into his eyes, reminding him to shut them again before the shampoo got in. Jimmy eased back up, sticking his head under the spray to scrub his hair clean from the bubbles. The rest of his body was cleaned quickly, he had all ready wasted enough time to still be in here. He cut off the water and pushed aside the curtains, wiping a hand over his face as he blindly groped for a towel. One leg out of the shower and then the other, still taking deep breaths through his nose as he toweled himself dry. He opened the door and went straight to his dresser, pulling on fresh clothes as he winced when his pants slid into place.

A short moment to recollect himself and he went over to his desk to get his papers and pencils, double checking for anything else he had missed. When he found none, he went over and down the stairs, taking his time with an extra twitch to his step as he went over to the living room. "Sorry you had to wait again.." Jimmy mumbled, going around the couch to give Dean a tiny frown. He stopped in front of the table and bent at the waist, shirt riding up as his sweats sagged low on his hips, revealing a patch of skin as he spread out the pile of worksheets neatly across the table. "These are my.. Failed assignments." Slowly, slower than usual at least, he straightened and turned around to sit down next to his teacher, chewing his lip rather hard as he let out a shaky breath.

It was a bit before Dean finally heard Jimmy walk downstairs. He frowned; the footsteps were... Off. As if the youth were walking funny. His suspicion was confirmed when the young man came into sight. He smiled politely and nodded in response to Jimmy's apology, then blinked. As the youth bent over the table, his shirt rode up, and Dean could tell his pants were hanging low. The patch of skin that was revealed made Dean swallow noticeably, and suddenly he felt like he shouldn't be there, at all. Temptation riddled his mind and he had to look away before the youth noticed as he sat down beside the teacher. He looked over at the assignments laid out before him and nodded. "Okay, pick one of these assignments and show me each wrong problem. We'll have your grade up to an A within two weeks if you work hard."

His eyes skimmed the papers, seeing a splatter of red marks decorate the while wooden surface. A piece of him grumbled and another sighed, his teeth dragging over his lower lip in contemplation. Jimmy leaned over across Dean's lap, his knee nudging the other's as he grabbed the farthest piece. The slight shift sent tremors through his body, his eyes fluttering close for a second as his breath hitched. "H- here." He stammered, sitting back with a clenched jaw and a firm grip on the paper. The majority of the sheet was marked red, a small grimace flashing over his face. "I've read over it a few times and I don't k- know what's wrong.." A faint pink bled into his cheeks as his breaths turned shallow. He bit his lip, trying to control his heartbeat that pounded like he had just finished a swim meet.

His breath caught in his throat when the youth leaned over him, automatically leaning back even though there wasn't much space. He felt a reaction with his body that tried to contain, and he hoped he succeeded; he breathed softly in relief when Jimmy pulled back, and he chuckled softly at the words spoken. He pointed to the first question missed and read the question out loud: "Which Roman Emperor was infamous for hating Christians and splitting the Roman empire into 2 parts?" He slid his finger down the paper to the answer that had been marked wrong, and he looked over at Jimmy. "You marked Constantine, which was wrong, of course. Can you tell me why?"

There was a moment of silence, his mind starting to drift away from what he was asked. His tongue darted out to wet his lips, drawing his eyes back over to Dean with a ragged breath. "It's wrong becau- ah! Shit." Jimmy squeezed his eyes shut and braced his arms on the couch, hands digging into the material as he hunched his shoulders. His face flushed red as he held back another gasp, squaring his jaw to keep himself quiet. Wait. Did he just _moan_ in front of Dean? His teacher? Footsteps stomped down the stairway, breaking his train of thought as he looked over to who it was. 

"Jiiiimmyyy, you know it's to- oh." Identical blue eyes stared at him, lips quirked into a smirk immediately. "You didn't tell me you had a guest over Jim, who is it?" A scowl was on his face the moment Castiel skipped over to lean in between him and Dean with a wide grin that crinkled the corners of his brother's eyes. "Oh! Hey coach, what are you doing here?"

His eyes widened in alarm when Jimmy suddenly seized the armrests, but before he could say anything, he heard a voice, much like youth next to him but quite a bit deeper. He blinked when the twin brother's face was suddenly next to his, and he could immediately feel his cheeks burning, knowing they were a bright red. "Well, Castiel, I-I was just tutoring your brother here. I'm sure you know he's failing History." He cleared his throat and scooted down the couch a ways, feeling quite embarrassed even though he wasn't sure why. It's not like he and his student had been doing anything.

A look of surprise over took Castiel's expression, he even made a small gasp and a disappointed frown. He looked at his brother, shaking his head slowly as they locked eyes, holding the stare for a few moments before it broke. A chuckle slipped out as he grinned, receiving a darkened look from his twin. "Of course I know my bother's failing. How could I not?" He drawled, reaching out to ruffled locks of thick hair to have his hand swatted away. "But Mr. Winchester, I have a question for you concerning him- do you know _why_ he's failing?" Castiel looked over with an innocent tilt of his head, rearranging his arms to fold on top of the couch to rest his head on, his body half bent behind the furniture. "I mean, Jimmy's smart. Really smart, and as a teacher I'm sure you know that even if his scores are the opposite."

A brow raised as he took in the way they looked at each other. Something more was going on here, but Dean couldn't figure out what. His other brow raised now at Dean's question, and he nodded slowly. "Yes, I know he is very intelligent. That's why I'm concerned that he is failing. Do tell me the reason, though, I'm all ears." Green eyes met blue ones, and Dean felt something within him stir again; he did his best to keep his blush hidden this time, for he knew what it was: his blood was rushing down south, all because he had looked into those gorgeous eyes. What the hell was wrong with him? These were his students, for Christ sake!

There were eyes in him, he could feel it bore into his skin. It was meant to stop him, he knew that, but all it did was motivate him. "Do you want to tell Mr. Winchester Jimmy?" Castiel looked over with the same expression, the question genuine though there was a flicker behind his eyes. His brother hesitated, looking down and prying his fingers off of the couch to place on top of his lap. Oh that wouldn't do.

"No? All right then, I'll tell him." He mused, turning back with a sigh. A hand moved up to allow him to lean against the palm, the other still rested and hidden from the teacher's view. His thumb rubbed over a smooth surface, toying over the plastic with a thought before flicking it discreetly. At the same moment he heard a sharp gasp, could practically feel his brother's uneasiness in the air. "You see coach, Jimmy's not really failing because he doesn't know the subject. No, he's failing it on purpose because we agreed on something. Isn't that right little brother?" His voice never faltered from the even tone, almost as if he was conversing about the weather. Castiel turned to see his twin tensed, hands balled into fists where it laid on his lap, arms tensed, and mouth hung open. 

"Y- yees."

A smug look appeared for a second as he shifted his eyes back over to Dean. "Do you want to know what we agreed on, _Mr. Winchester_?"

His eyes never left the other's face until he saw movement in the youth's hand and heard the audible gasp from his brother. Shit. Was that the controller to a vibrator? That was inside Jimmy? That _Castiel_ controlled? Dean knew then what he'd gotten himself into, and he gulped, though the idea rather... Well... They'd be able to see for themselves if they looked down at his lap. "To get me alone. Here. In your house." Christ, what an idiot he was, to allow himself to fall into a trap like this. Just the thought of being alone with the two twins... Fuck, fuck, fuck. He didn't think there was a way of getting out of this, and he wasn't sure he wanted to get out of it.

A delighted look beamed on his face, a smirk stretching wider as he nodded. "I knew not all teachers were dumb. You see, that's part of it. I told my little brother that if he could get you here first then, well, I'd let him get fucked first. Isn't that right Jim?" Castiel purred, looking over with a devious grin as he hit the button again, dialing up the setting. 

Jimmy let out a throaty moan, slumping forward slightly at the change, gasping unevenly as a hand shot out to grip his arm. " _Yes_." He rewarded his twin with a comforting touch to the hand that was grasping him. 

"And who did I say you could be fucked by?" 

Black blown eyes shifted from him face over to Dean, locking on the man's face. "Mr. Winche- eahh! Winches.. Terr." 

Castiel nodded, looking back at Dean through thick lashes, letting his eyes rake down Dean's body, down to a bulge in the man's dress pants. "Exactly. Would you like that coach? Would you like to fuck my baby brother first and then fuck me?" There wasn't enough time for him to hear what the other would reply with. Not when he had leaned down to capture his twin's mouth with his, nipping and tugging at ebony hair. Jimmy moaned and whined, parting pink lips easily as Castiel swallowed each one of them, darting his tongue out to lick his way in.

Oh dear sweet Jesus. This was... this was beyond any fantasy he'd had before. This was the king of all sexual fantasies. Seriously, who _wouldn't_ wanna fuck twin brothers? He watched with eyes dilated with instant lust as the two kissed right front of him, his hand sliding over to palm himself through his pants. Hell, he was already hard as fuck. His voice was incredibly husky when he spoke. "You have no fucking idea." And with that, he lunged forward on the couch to grab Castiel's shirt, making him wrench away from his brother. If there were any sounds of protest, he didn't hear it, as he now claimed the boy's lips with his own. The youths wanted to play? Fine. He would show them exactly what it was to get into it with an experienced adult.

The two protested in unison, Jimmy with a pitiful whine and Castiel with a sharp grunt that was silenced immediately. His eyes slid shut as he found himself kissing a different set of lips, soft yet firm, pressing against his with determination. Castiel untangled his fingers from his brother's hair, moving it to snake up Dean's neck with a long moan. There were soft noises next to him, ones that he knew too well that sent a wave of arousal through him. He flicked the dial up another notch in a silent apology of the shortened attention, knowing he was forgiven with a low keening noise.

Watching his brother make out with his teacher definitely was _not_ fair. But any sort of complaints he had died down when the vibrations in him quickened. "Fuck." Jimmy ducked his head, digging his nails into the couch again as he strained his neck. It felt so good, the constant vibrations hitting directly on his sweet spot that sent hot sparks through him. "Ca- aaaaaaass." He whimpered, taking a shallow breath as he cracked an eye open to watch the other two.

Damn, the boy could kiss. He groaned softly against the youth's lips before pulling back with a slight pant, taking in Castiel's expression before shifting his attention to the other brother. A smirk flickered across his lips as he carefully moved forward to press them against Jimmy's, his tongue tracing the bottom one before he shoved it into the other's mouth, groaning softly as he tasted the youth. God, he'd never tasted anything as amazing as these two, and he was clearly about to get super lucky with both of them. He lifted his hand to cup the youth's cheek, his fingers slightly sprawled out over the skin. He couldn't think past the raging boner in his pants and the explosive taste that was the inside of Jimmy's mouth. All he knew was that he wanted the twins, and he wanted them _now._

His lips eased open without hesitation, eyes already half lidded as he moaned into the lips that pressed against his. It was different, the way their tongues tangled, hot and spit slick, almost similar to the way he kissed. He could tell it wasn't Cas just by the way the man roamed, a hand caressing his cheek while his brother preferred to tangle fingers into his hair and tug. Jimmy allowed himself to be draped by a larger body, inching back towards the couch arm until he was pressed against it.

It was Castiel's turn to watch now, eyes lust blown as he licked his lips slowly, memorizing the way Dean had kissed him. How sweet and new it was. He took off his shirt and pants, leaving his boxers on as he threw it over on the ground somewhere. "He has a vibrator in him, been all loose and stretched since he got home. You can fuck him right now if you want _Dean_." Castiel purred, voice dropping to a gravelly timbre as he leaned over to mouth at the man's earlobe.

He had backed Jimmy easily into the arm of the couch, his free hand moving to rest on the youth's crotch, his palm pressing lightly at first as he continued kissing the boy. But when heard Castiel's words and - _Jesus_ \- the youth's lips on his ear, his palming roughened, and a groan sounded in his throat as he kissed Jimmy. Finally he broke away, panting as he locked eyes with Jimmy. He shifted backwards, the hand that had been palming the boy lifting to run through Castiel's hair, and still his eyes didn't leave the other's. "I want you naked and on your hands and knees, Jimmy," He growled in his lust-husked tone before he turned his head to claim the less shy boy's lips once more, kissing him exactly the way he'd just kissed Jimmy. He hadn't noticed yet that Cas had stripped, but boy, was he in for a surprise.

His head tilted back as a breathy whimper curled under his tongue, caught in his throat as he jolted at the sudden touch. Everything felt so damn good, the pleasure doubled by the vibrator and just the simple fact that this is _Dean_. Jimmy snapped his eyes open at the loss of touch, mouth still parted as he whimpered. Scratch that, as he swallowed thickly with a soft moan, nose flaring as he bobbed his head immediately. The clothes were discarded in record time, all flung to the opposite side of the room as he scrambled to do as he was told. He turned around to kneel down with his hands planted below him, legs spread as much as they could to present himself to the other two.

A shiver ran down his spine at the way Dean spoke, drawing an approving growl from his chest as he complied to the kiss. Wet and hot, almost similar to Jimmy's and opposed to his skill based tactics. Castiel ran a hand through cropped hair, tugging at the bottom as he snaked his tongue up to the roof of Dean's mouth. He let his tongue trail slowly across the surface, moaning without shame as he tilted his head to deepen the kiss.

He held the kiss he had going with Cas- it was too fucking hot to break just yet- but he peeked open an eye to glance at Jimmy out of the corner of it. He almost came right then and there. The sight before him was absolutely beautiful and worthy of a porn video, and fleetingly he wondered if there were any cameras set up somewhere. But he didn't give it another as he let his eye fall shut once more, moaning softly into Castiel's mouth. The way the youth's tongue felt was mind blowing, and he couldn't help but give the boy's hair a small tug, a growl sounding in his throat. When he was finally able to pull away from the kiss, he smirked, letting his tongue swipe across his lips as he stood and slowly began unbuttoning his shirt. "I bet you wanna watch me fuck your brother, don't you, Cas? You wanna watch me pound into him, over and over, so that you can see what's in store for you." He was extra slow with each button, his eyes never leaving the youth's face.

Oh this man was good. _Very_ good. His eyes slid open and watched the man lick his lips, running over the full flesh of the lower lip. "Oh, I have a pretty good idea what to be expecting Dean. But Jimmy's first, he's been a good baby brother and deserves to be the main spot of attention." Castiel drawled, eyes glued to each button that was popped at an unnecessary slowness. "You can fuck him, and I'll watch. Of course I'd watch." His hands shoved down his boxers, the fabric pooling around his ankles as he stepped out of them. He walked around the couch slowly, fingers trailing along the top of the furniture as he adverted his gaze to look over his twin. "With Jimmy sucking my cock at the same time." A wolfish grin spread across his face, feet stopping directly in front of his brother. His heated member hung proud and heavy, swollen crown already pearling precome. "You know what so good about my brother? He has this whole shy and bashful manner to him, all blushes and nervous fidgets. But that's not really you isn't it baby boy?" Castiel combed his fingers through Jimmy's hair, bringing his brother closer to his waiting cock. "You're always thinking dirty things, wanting to get fucked all the time and be a good little cocksucker. Always do what you're told, so _responsive_ to everything."

His arms trembled at the words, eyes flickering down to hone in on his brother's member, inching forward to nuzzle against the base. Without being told he flicked his tongue out, licking a long stripe up to the tip and swirled his tongue around, tasting and savoring the other. Jimmy parted his lips and sank down all the way, not even gagging when the back of his throat was nudged. "Oh _fuck_ , you're so good at this." He heard, moaning his opinion in response as he began to bob his head, hollowing his cheeks as much as he could.

There was no way Dean could take his clothes off slowly, not with the show he was getting. Before he knew it, he'd stripped himself of every stitch of clothing and he now positioned himself behind Jimmy, sitting just between his legs, nudging them apart a bit. He leaned down to whisper into the youth's ear: "You are a good listener. Good. Keep it up and you'll be getting an A in no time." Dean whispered as he ran his fingers up the younger male's spine. He pulled back to take a look at the rear, grinning when he saw the vibrator. He removed it slowly, very slow so that Jimmy would feel it before he tossed the device behind him and lined his rock hard cock up with the now wide open entrance. His eyes locked with Castiel's across from his as he slowly slid himself inside Jimmy, only a thin line of green showing with how dilated his eyes were. Once he was sure Cas had gotten a good show out of it, he leaned over the youth he was inside to claim the other's brother's lips in a rough kiss, his hands gripping Jimmy's hips as, without warning, he began to snap forward in a quick pace, so that every time he thrust in, the youth's head bobbed on his brother's cock.

Overwhelming, it was utterly, perfectly overwhelming. A high moan came out of his as he felt the vibrator inch out, scraping over the bundle of nerves that shook him down to the core. He didn't have time to whine when he clenched down on empty space. Not when something bigger and hotter was slipping inside of him with no resistance. His words were muffled as he keened, screamed when he was filled, Dean's cock stretching him to the fullest. He didn't know if he should shove back or go forward, both holes filled as he was rocked and pounded on to create a synchronized rhythm. Fingers bit into cushions, knuckles pale white as he sucked his brother with more vigor, spurred by the thrusts he was receiving from Dean.

Everything was taken in- the sight of the Dean's cock nudging its way in, the wanton face of his brother sucking his cock like a whore, everything. When Dean had leaned in, he followed, crushing his lips against the other's. He groaned at the immediate urgency, the slight bump of teeth, and the fight for dominance. Jimmy sucked harder, dragging a throaty moan out of him as he snapped his hips forward, knowing his brother could take it all. His hand rested on the back of his twin's head, keeping him in place as they all moved together, pleasure coursing through his veins like wildfire.

The moment of clarity that was bound to come finally struck, the thought 'I shouldn't be doing this to two teenagers, fuck, I'm in so much trouble' running through his mind. He shut it down immediately, losing himself in the twins, in Jimmy's - still - tight, hot, deliciously wet hole, in Cas' equally hot and delicious mouth. The youth was definitely the more dominate of the two brothers, but Dean knew he trumped both of them when it came to kissing. He quickly took over the kiss, pushing back as he shoved his tongue into Castiel's mouth, loving the taste that was so like Jimmy's and yet was Cas' own. These two were bloody amazing, and a piece of mind couldn't believe how lucky he'd gotten. His pounding only got rougher and rougher, his sack slapping against that cute little ass with each thrust. Dean lifted one hand to slip around the back of Cas' neck, holding the youth there as they kissed.

Tears were starting to well at the corners of his eyes, his breathing shallow and ragged. Out of all the things that he had done, this was by far the best- everything about it was. Jimmy let lose a continues string of mewls and keening sounds, knowing that each noise he made was sent straight down his brother's cock. With each thrust, the quickening pace of being fucked, he squeezed a little tighter, wanting to feel hot come pour into him.

It was his pride that got in the way, the usual mind set that he was the one that dominated. At first he fought back, tongues clashing viciously to see who the victor was, but he slowly gave in. He had experience, a lot with what he had done with his brother but for once he was stumped. His advances became more subtle, letting Dean do what he wanted as he just followed. Castiel curled his hand tighter in his twin's hair, knowing that if this kept up, he'll be coming soon, really soon.

Already he was close, so close, his cock throbbing within Jimmy. God, the younger male felt so good around Dean, it was amazing he hadn't come already. But with the way the youth was clamping down around him, he knew he wouldn't be able to last much longer. And with the pornographic kiss between him and Cas still going on... This had to be the best day of his life. No, this /was/ the best day of his life, and he didn't want it to end, at all. His fingers slid up into soft, dark hair as he twisted his tongue with Cas', almost as if the two were dancing in the younger's mouth. He wondered how much longer the twins would last, knowing it couldn't be long now; the boys had to be as close as he was at this point.

All it took was an expert flick of the tongue around the head of his aching cock and he was swearing every single curse word he knew in his mind. His hand was fisted in thick locks, his hips a fraction away from pounding into his brother's glorious throat with a litany of moans and soft growls. It took the feeling of a hand twisting in his hair, sending small spikes of pleasure down to his throbbing member, and another swipe over his slit and he was seeing stars. Castiel shut his eyes and gaped, paused his movements as he was thrown over the edge with a hard suck from Jimmy. His body convulsed and tensed, come pouring out to be sucked by his twin.

Just, a little bit more and- Hot liquid shot down his throat, his eyes widening as he swallowed it all down eagerly as he gasped around Castiel's pulsating member. His body locked up all at once, his ass squeezing tight around Dean as he felt his body shake. White painted a part of his stomach and the couch below him, his arms nearly collapsing as Dean continued to pound into him.

The moment he felt Jimmy clamp down around him, he released Castiel's mouth with a loud groan, though he didn't let go of the youth's hair. Within moments, his seed was spilling into the twin beneath him, and he had his lips latched onto the neck of -he assumed- the older brother, sucking roughly as he emptied his load into Jimmy. He sort of slumped against the kid's backside even as he worked on the hickey that would mark Cas as his, a growl sounding in his throat. When he finally let go of the older brother, he panted softly as he leaned down to press kisses along Jimmy's spine, his words coming out in whispers. "So perfect.. such a good little student.."

A side ways grin spread across his lips as he heard that noise, a throaty growl that made him curl his toes. The hickey wasn't unnoticed as a sense of delight ran through him at the marking. He let out a heavy breath as he stroked his twin's face, pulling out as his cock softened. "Come here Jim." Castiel knelt down to be leveled with his brother and kept his hand cradled on the side of the other's face. Without a word he pressed forward, licking at the remnants of himself on plush lips that opened immediately. It was slow and languid, both riding out the end of their release. For a second they forgot Dean was here, too caught up in the lazy exploring of each other's mouths. It wasn't until Jimmy dipped his back a little did Castiel part, looking over his brother's shoulder at Dean. "So what do you think teach? Can Jimmy pass your class?"

Dean pulled back just in time to watch the two brothers kiss like their lives depended on it, and boy, if that didn't strike up arousal. He slowly pulled out of Jimmy, his eyes still dilated with lust as he watched, his tongue flicking across his lips. When they parted, he could see just how red Castiel's lips were from kissing his brother so hard, but he didn't dwell on the sight; his eyes found the other's and he gave one of his usual smirks. "Only if he promises to stop failing on purpose. If you wanted me over, all you had to do was ask. And now, I believe its someone's else turn, isn't it?" He grinned as he leaned over the younger brother carefully to capture Castiel's lips in a kiss, the meaning of his words lingering behind it. He could feel the way his still hard cock pressed into the cleft of Jimmy's ass, and god, the youth felt so good, he couldn't help but wonder how the other would feel. The thought immediately struck heat down into his groin, and he groaned against those soft, plump lips, loving the taste of them quite immensely.

With one small gesture, he smiled into the kiss, soft compared to what he had just done. Castiel withdrew to give a kitten lick across the seam of Dean's lips, smirking as he leaned back. "You know what to do little brother." There was a nod from his brother as the two moved, Castiel walking over to stand in front of Dean as Jimmy stepped aside as he sought out the discarded vibrator. "As much as I want you to fuck me right now, I haven't had the time to prep myself." He placed his hands on Dean's shoulders, pushing the man up to flatten his back against the couch. "And while Jimmy's going to plug himself with his vibrator, what do you say to me sucking you cock hmm?" His hand skimmed down Dean's chest lightly, leaned in to mouth up the man's neck to whisper in the other's ear.

He purred softly under Cas' little lick, but was surprised when Jimmy moved away and suddenly Cas was in front of him, Dean's back pressed against the couch. His eyes dilated to their fullest once more at the older sibling's words, but before he could respond, he cut himself off with a light groan as the youth lipped at his earlobe. He could only imagine what Jimmy looked like as he was pleasured with the vibrator, and that image combined with the one of Cas sucking him off made his cock twitch. He nodded quickly, his breathless words tumbling out into the air. "Yes, god yes, please." He rutted his hips against Cas' once to show just how much he wanted it, so bad that he would have shoved the kid down on his knees right then and there if his thoughtfulness hadn't taken over.

A soft chuckle slipped from him as he felt Dean buck against him, his eyes narrowing to slits. "How polite, you asked please." He murmured, placing an open mouthed kiss underneath the other's jawbone. The man's scent was simply mouthwatering. Whatever cologne Dean used mixed with his natural scent and the faint smell of sweat made him lick his lips. "You don't have to be so courteous with us Dean." Castiel hovered over the spot he had nipped at, licking over it once before trailing down the neck. Each kiss and lick made its way down lower, traveling from the collar bone down to the man's navel and eventually, to the base of heated skin. "You ready baby boy?" His tongue darted out lavish the length before him, his lips wrapping around the head as he swirled his tongue around the crown. He didn't need to look back at his twin, already knowing that his brother had heard him. In one fluid motion his jaws parted and he took Dean down in one bob of his head. His eyes fluttered shut as he swallowed around the thick cock, thinking of how it would feel in him. He sucked up, letting his teeth graze the vein that was pressed against his tongue as he hollowed his cheeks.

Where the damn thing was, he didn't know. He only knew that he needed to find it quick before Castiel started without him. With a few seconds of shuffling, the pink vibrator was spotted and grabbed. Jimmy looked over just in time to see his brother on his knees, sucking Dean with a look that made his softened cock twitch. He slipped the vibrator back in, wincing slightly as it was pushed against his prostate. But he didn't have time to play with it, not now at least. Jimmy went over to kneel behind his brother, palming each cheek before he spread the other's ass. He leaned forward and licked over the hole, feeling it flutter under his tongue. Normally he would drag it out longer, prod and rim his brother slowly until he was told to 'just fuck him' already. But instead he sucked on two fingers, slicking them before he pressed against Castiel's hole, easing them in up to both knuckles.

Dean's eyes rolled back in his head, each kiss sending a small yet still erotic tingle of pleasure through him. When he felt that lovely pink tongue on his heated flesh just above his cock, he almost bucked his hips, but he didn't want to seem like an eager slut; he was about to be blown by a teenager after all. A sexy, gorgeous teenager with an equally appealing twin brother, but still, both teenagers. He couldn't help the moan he let out though when those perfect lips wrapped around his head, and then the gasp when the boy took him in all the way in one swallow. His hands immediately flew down to the youth's shoulders, gripping them rather tight as he practically chanted "Fuck, Cas, aah, fuck" over and over. And then.. oh god, was Jimmy about to fuck his own brother? From the visual Dean was getting, it sure seemed like it, and this time his moan was amplified in volume, the teeth grazing the vein in his cock making him shudder. "C-Cas, fuck.. feels so good.." He managed to groan out, his speech ability marred by his breathlessness.

Just hearing those two made him hard in a minute. Plus the tight hole he was fingering and the stretch of the vibrator that plugged Dean's come in him. He slipped a third finger in along the other two, moving his lips along the flesh of Castiel's ass to place small kisses and nips. All he could manage was a few more minutes, enough to loosen his brother but not enough to stretch him completely. Jimmy scooted closer on his knees, retracting his fingers to lick a stripe across his palm and slick himself hastily. With one hand at the base of his cock and the tip pressed and nudging into his twin, he snapped his hips forward to bottom out in one thrust. "Oh _fuck_ " He groaned, running his hands along Castiel's sides as he set a slow pace, relishing the feeling of the tight heat.

Castiel flat out moaned like a bitch in heat when he felt fingers stretch him open, one by one until a cock was shoved into him. His sucking only grew more insistent, eyes opening to look up at Dean. It was lewd, the way he sounded while getting fucked by his own brother and sucking his teacher dick, but so _good_. Every thrust was punctuated with a short gasp and swallow around Dean, his mind hazing into a mess. But he stopped, pulled off of Dean with a wet pop as he tapped his brother's arm twice.

He could feel the difference in just the couple of nova Cas had given him and the more jerky head movements that went along with Jimmy's thrusts, but it all felt so amazing that Dean didn't care about the difference. He moaned with each bob and groaned when Cas suddenly pulled off. 

"I said, that, you would fuck me right?" A grin stretched across his face as Jimmy slipped out, allowing him to slowly climb on top of Dean to straddle the man. "And if I come before Jimmy does watching us, then I'll eat your come out of his ass." Castiel licked his lips slowly, lifting himself up to grind back against Dean's cock.

As soon as the words were said, Cas was in his lap, grinding against him, and it was all Dean could do to hold himself together as he seized the youth's hips, growling as he eagerly returned the grinds. He leaned in close to Castiel's ear, his voice pitched low and even huskier than before; he knew it would sound like pure sex. "I hope you know what you're getting yourself into, boy. What Jimmy just received? It's double when riding me." Dean smirked, flicking his tongue along the shell of the youth's ear before pulling the lobe between his teeth; it was his turn again to leave marks, and he intended to leave plenty of them. His hands slid up the boy's naked torso, their sweat slippery bodies grinding roughly together as he felt the youth up, growls punctuating his kisses and nips.

It would be a terrible lie to deny the fact that he shivered at what Dean said. His teeth dragged along his lower lip as hands and lips roamed the planes of his body, feeling and tasting every inch of skin. "Oh yeah? Prove it." Castiel canted his hips up, reached back to line Dean up to his waiting hole. Dean would be bigger than Jimmy, he knew the man would be when- "Holy _shit_." He felt the raw burn as he lowered himself onto Dean's cock, gasping as he went down to the hilt.

After he had pulled out, he knew it wouldn't be long until the other two would start fucking. Waiting wasn't in Castiel's nature. He got up and went over to sit on the couch, swiping the control as he sat down to watch his brother and teacher grind against each other. The switched was flipped and the buzzing came alive, vibrating right against the bundle of nerves that shot pleasure through his veins instantly. Jimmy settled back against the arm if the couch and spread his legs. He couldn't touch the vibrator, but he could touch himself. His hand wrapped around his member, automatically pumping as he saw Castiel sink down on Dean's cock. A moan slipped out as he watched, eyes greedily drinking in the sight.

He still had his lips on one side of Castiel's jaw, but when he felt the youth slide down on him, he released a wanton groan against slick, heated skin, the way Cas felt around him absolutely blowing his mind. Even with the fact that he had already been loosened up somewhat by his brother, Cas was still amazingly tight, and Christ, he felt so good that Dean wanted to switch their positions so that he could pound into the youth like there was no tomorrow. He could the other brother across from them moaning as he pleasured himself, and he couldn't help but let that be a motivator as he immediately began moving his hips upwards, his growl more guttural as he nipped at Castiel's jaw, hands continuing to skim over the youth's body.

Being on top was something he had perfected, something he had trained himself to become a master at just like how he had trained Jimmy to be the perfect cockslut. The person underneath him wouldn't move, not when he was fucking himself down on a cock with his hands planted on the other's chest. But Dean didn't play by that apparently. A surprised gasp was sucked in sharply when he felt the cock ride in deeper, shuttering as he paused for a split second. His brows furrowed as he tried to focus on taking control, to make it so that Dean wouldn't be able to move but it was getting extremely hard to not just submit and let him be fucked over and over from the top. Castiel slid his eyes shut, hating the amount of pleasure he felt from riding the man when he wasn't the only one taking the reins.

Oh. That was rare. His hand never stopped it's course as he watched the other two and he couldn't help but feel a thrill run through him at the short stop his brother had come to when Dean had moved. The only time Castiel had ever stopped moving when on top was when the person below him was too good for him to control. Jimmy licked his lips slowly as he let that play in his mind, as he remembered what it was like to be fucked by the older man and to have his come plugged within him. Shit.. He clenched his jaws at the slip of his hand, trying his best to keep the orgasm at bay as he pumped a little bit slower, wanting to outlast his brother.

God, Cas felt and looked so good on top of him... Dean couldn't resist thrusting sharply, repeatedly into the younger boy, his teeth gritted and his hands keeping a tight grip on the youth's hips. He could feel Cas trying to take control, to keep his coach still beneath him; Dean wasn't gonna have any of that. The older man could hear the younger brother across from them, he could hear the sound of skin moving against skin, making a wet sound that sent a stab of heat down into his groin, and in reaction, he groaned loudly, his eyes squeezing shut as his thrusts hardened and quickened. 

There wasn't even a second for him to even think that he had quelled the man below him. Not when his eyes snapped back open and a choked noise came from his open mouth. "Holy _shit_." Castiel scrabbled to keep himself latched to Dean with his nails digging into the man's chest as his breathing came in ragged gasps. Not only had the pace quickened, but Dean had also somehow found his prostate and was hitting it in perfect aim repeatedly. Tears pricked at his eyes from the overwhelming growth of pleasure, and he didn't even have the chance to try and stop the thrusts before he shouted. The sheer force of his orgasm made him double over, his body shuttering as come coated his lower abdomen. The room spun for a few seconds as the ringing in his ears hammered with the pounding of his heart in unison, droning out anything else.

Just as he was about to shift his position, the need to disappeared when he heard that sound from Castiel. One that he knew too well and usually ended with his face shoved into his brother's crotch as come poured down his throat. Jimmy stared wide eyed at the pair, disbelieving at how fast it had taken for his twin to orgasm. His hand moved even faster, gyrating at the head as he focused on just the pure sense of pleasure that ran through his veins. Another three seconds and he was pitching in his own broken moan, head tilted back with his lips parted and eyes half closed.

He didn't have time to even think when he heard Cas yell and he felt warm liquid spew onto his abdomen, undoubtedly painting the youth's torso as well. Deab couldn't believe he'd made Castiel cum so fast, and it was clear by the sounds Jimmy was making that he'd hit his peak too. It was all too much for him, and he couldn't hold back. His fingers dug into the boy's hips as he hollered, his thrusts ceasing and his body becoming rigid as he spewed his seed into the young teenager on top of him.

When he'd finally been emptied of his load, he loosened his grip on Cas, gasps escaping him as he tried to catch his breath. He stared up at the younger male, his pupils still blown wide with the intense desire he held for the two boys, and he spoke between breaths, "You.. are too.. fucking sexy. Fuck."

Castiel blinked a few times to clear out his head with barely enough strength to keep himself up on shaky arms. "You're... not too bad.. yourself." He weakly chuckled back, avoiding the thought of how fast he had came. Regardless of the time, that had to be one of the best orgasms he had ever had. The wanting to lay down and pass out was strong, but somewhere in his fogged mind, he remembered the bet he had dared to place before his release. "So.. Looks like I lost huh?" He managed to grin and turn back to look at his brother who was as equally worn out as he was. "Turn around Jim."

Jimmy blinked blearily back at his brother, taking a moment to ride out the pleasure that was quickly depleting. Soon he was shuffling around to drape the top half himself over the couch arm and present his ass towards the other two. The vibrator was still on and it was getting to the point of it being irritating, but he didn't dare to remove it without his twin's say so.

"Good boy." He purred, untangling himself from Dean and to lean over. His brother's hole was puffed around the purple end of the vibrator, and he took his time in running a thumb over it just to see Jimmy flinch a little. Slowly, he pulled it out only to drop it onto the floor as he dived in before any of the substance could leak out. Castiel couldn't help but groan as he lapped the come out of his brother's ass, using his hands to spread the cheeks more for better access.

 

With a soft groan Dean pulled himself up to have a better view of the two Novaks, groaning once more when he saw how into it Castiel was. Words failed him as he simply reached out to run a hand over the swell of the older brunet's ass. 

Castiel pushed back when he felt a hand on him, moaned as he pushed his tongue in deeper. Eventually he leaned back, satisfied as he licked his lips before he was pulled back onto Dean's lap. Their lips met and he purred into the kiss, lazily licking and mixing their tastes together. He pulled back, breaking the kiss to beckon his twin over to curl up on him as he shifted around to lay down in a more comfortable position. 

Words couldn't even describe what had just happened. To him, the teacher of one of these boys and the coach of the other. Still, his mind was too fried to even worry about the best sex he just had in his life. Dean gave a content sigh as he watched Jimmy and Castiel cuddle up on him and ran a hand through the eldest's hair. 

“Can you tutor Jim again sometime soon?”

“I can give you two a ride home tomorrow. Deal?”

“Deal.”


End file.
